Tandem Synthesis of α-Diazoketones from 1,3-Diketones

Jianlan Zhang, Wenwen Chen, Dayun Huang, Xiaobao Zeng, Xinyan Wang* and Yuefei Hu*

*Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China, Email: wangxinyanmail.tsinghua.edu.cn, yfhmail.tsinghua.edu.cn

J. Zhang, W. Chen, D. Huang, X. Zeng, X. Wang, Y. Hu, J. Org. Chem., 2017, 82, 9171-9174.

DOI: 10.1021/acs.joc.7b01187

---

Abstract

The reaction of 1,3-diketones, TsN₃, and MeNH₂ in EtOH enables a highly efficient synthesis of α-diazoketone via a tandem reaction including a novel primary amine-catalyzed Regitz diazo transfer of 1,3-diketones and a novel primary amine-mediated C-C bond cleavage of 2-diazo-1,3-diketones.

see article for more examples

proposed mechanism

---

---

Key Words

α-diazoketones

---

ID: J42-Y2017